Taking Chances
by TroySharpaySharpayTroy
Summary: So, I was thinking and what if Troy hadn't gone after Gabriella to Stanford what if he had accepted she was gone and turned to an unlikely person...
1. Rooftop Meeting

**So, I was thinking and what if Troy hadn't gone after Gabriella to Stanford what if he had accepted she was gone and turned to an unlikely person... thank you to my beta disco-wing**

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Sharpay didn't tell Troy about Gabriella's Stanford opportunity to get revenge or out of some plan she was forming in her head. No, she told him because he deserved to know the truth, that little Miss Perfect was bailing at the end of senior year. She had left yesterday and Sharpay was walking the halls of East High beaming. She wouldn't have to hear Gabriela's annoying as fuck voice. She wouldn't have to see her throw herself onto Troy. And she wouldn't have to watch her raise her hand to answer every question while looking like she was going to piss herself if the teacher didn't call on her.

The other students were acting like their kitten died and that life was over. Sharpay never understood why everyone was so fucking obsessed with Gabriella Montez. On her way to rehearsals, she saw Troy heading up to the roof. Probably on his way to the spot that he and Gabriella shared. Making a split-second decision, she decided to follow him.

"So, Bolton, up here moping about your girlfriend?" she asked, sitting down next to him.

"You know I told you because you deserved to know. I know this won't change anything or make you want to be with me. It was just shitty what she was doing to you, acting like you're stupid," Sharpay confessed.

Troy sighed, "I'm not mad at you Sharpay, I'm grateful someone had the balls to tell me the truth. Now Gabriella's saying she may not even come back for Prom or Graduation, it was always about her dreams and what she wanted. She never even considered asking me about what I want to do with my life," he replied angrily.

"Well at least you have a date to Prom, Zeke keeps asking me, but I would rather stick pins in my eyes than go with him," she said with a heavy sigh.

"See Sharpay, that's what I like about you, you are unapologetically yourself. I keep letting my friends tell me what's best for me, and let them make me feel bad for following my heart. I wanted to sing with you over the summer, I feel so bad for what I did and how I've ignored you all year because of them. I've been such a pussy." he confessed sadly.

"Following your heart?" Sharpay questioned, rolling her eyes, "You mean not being a little bitch that tries to please everyone. It's your life Troy, you should do whatever the fuck you want."

Troy loved how brutally honest Sharpay was. She knew him so well. She was like a breath of fresh air and without thinking he pulled her into a kiss, the kind of kiss that makes time stop. The kind of kiss you get lost in. Sharpay knew that nothing would come from this kiss, that nothing would change, but she was going to enjoy it while it lasted.

When the kiss ended Troy looked at her, "Sharpay, I feel like I was supposed to be with you last summer. Like it was fate or some magnetic force pulling us together, I know I'm technically still with Gabriella, but I want to give us a shot see if this is something that will last beyond high school. You make me want to go for what I want and not be sorry for doing it." he spoke passionately, "And if it turns into something more, I'll break up with Gabriella the next time she's in town. We'll even go to prom together."

Sharpay was speechless, for the first time in her life, Troy Bolton wanted to be with her.

"I don't want to be some dirty mistress Troy, you broke my heart last summer and I refuse to let you do it again. This better be real, you can't go run and hide if your friends find out or change your mind if Gabriella cries." She exclaimed, "We only have a few weeks of school left and I want them to be fucking memorable."

Troy felt his phone vibrating in his pocket but chose to ignore it, "You aren't a dirty mistress or a rebound. I think you are just what I need in my life and it's taken me this long to finally realize it. Sharpay Evans, will you go to prom with me?" he asked hesitantly.

Sharpay sat there for a moment, letting him sweat, and tried to look like she was deep in thought.

"I guess I can go to prom with you Bolton," she said pulling him into a kiss.

They spent the rest of the school day on the roof talking and coming up with ways to be together before he broke the news to Gabriella.

What they didn't know however, was that Gabriella Montez was heading back to East High. She kept calling Troy, only to reach his voicemail.

"Hey, Wildcat it's me. I'm so sorry for just leaving you like that. I'm coming back to East High, I'm giving up the honor's program to finish up the year with you and our friends. Call me back when you can, I love you"


	2. Fallout

Thank you again to my beta disco-wing

After Troy and Sharpay parted ways for the evening, he finally checked his phone to find missed calls and texts from Gabriella. When he listened to the first voicemail, he thought he was going to be sick, she was coming back for him and to be with him. Then his mind instantly went to Sharpay. About how he told her he wanted to give them a shot. That she was more than a side piece, a dirty little secret.

Her texts told him that she would be back at school in the morning and she couldn't wait to see him, he knew he should tell Sharpay, but he couldn't do it. He couldn't have that kind of talk with her after the great day they spent together on the roof. He shut off his phone and got in bed, spending the entire night tossing and turning, waiting for the dreaded alarm to go off.

Sharpay on the other hand felt like she was on cloud nine. She was going to be with Troy, and Gabriella would finally not be around to ruin everything. She got ready for bed so excited for school in the morning. Little did she know she would soon regret it.

Troy pulled up to East High and saw Gabriella standing in the parking lot with their friends waiting.

"Fuck," he said before putting a fake smile on his face and getting out of the car.

Gabriella ran over to him and jumped into his arms just as Sharpay was pulling up in her pink car.

She slammed on her brakes and put her car into park the second she saw Gabriella in Troy's arms.

"This is not happening right now," she said to herself. She obviously couldn't flip out because then she and Troy would be outed. But seeing the guy she was supposed to spend the morning with back with his ex, made her feel sick. That stupid bitch ruins everything.

Sharpay got out of the car and walked by Troy her heels clicking. She glared at him with a look of rage and sadness, tears welling in her eyes, but she refused to let anyone see her cry.

"Hi Sharpay!" Gabriella said holding Troy's hand.

"Go fuck yourself Montez" she said brushing past her and heading for her locker.

Troy saw how hurt she was and knew things were going to boil over, but Gabriella looked so happy he couldn't break up with her yet.

"What is her problem?" Gabriella said sounding a little hurt, "I didn't do anything to her" she added.

"You know Sharpay" Troy said. "You didn't do anything, she's probably just having a rough morning" he added, walking into the school with Gabriella.

Everyone was so excited to see the golden couple back together.

Sharpay was at her locker trying to calm herself down, "He wants to be with you" she said to herself "He just needs to find the right time." She slammed her locker door shut when she heard Troy.

"Baby I'll be right back," he said kissing Gabriella on the cheek and pulling Sharpay into an empty classroom.

"What the fuck do you want Bolton," she said pulling her arm away from him, "I'm such a fucking idiot" she said stomping her foot. "I actually thought you wanted to be with me. We had a perfect day yesterday, and I show up to school to find Gabriella back in town and all over you like she did nothing wrong. Like she didn't crush you. That all of the things you told me yesterday never happened?" she said. "You didn't think to call me, prepare me?"

Troy could see the hurt on her face and it was killing him "Shar, I didn't know she would come back, I didn't want to tell you this over the phone, she was so excited I couldn't break up with her today." he said knowing how bad that sounded.

"I see how it is, I'm good enough for you when she's not here." she said "Good to know before I put my reputation on the line for you, and you with your following my heart bullshit. I can't believe I fell for it. I keep letting you hurt me over and over hoping something will change."

"Shar I'm sorry. I want to be with you I just can't right now give me some time," he said knowing what an asshole he was.

"You are the most selfish person I've ever met Troy Bolton and that's coming from me!" she said slapping him and running out of the classroom to the bathroom in tears.

Troy walked out of the classroom to find Gabriella, "Can I walk you to homeroom?" he said taking her hand.

They took their seats and Sharpay came into the classroom, her eyes puffy and took her seat. She spent the entire class staring at the wall trying to tune out Troy and Gabriella talking about prom and being vomit inducing levels of cute.

"Why is she crying?" Gabriella whispered to Troy "Did Starbucks mess up her order this morning" she added with a laugh sounding really bitchy which had Troy taken aback.

"Gaby stop just leave her alone she has a lot going on ok" he said suddenly realizing he was a dumbass he was.

"Since when do you care about her?" Gabriella said as the bell rang and Sharpay whipped past them.

When it was finally time for lunch the wildcats took their spots at their usual table, and Sharpay sat by herself at a table next to them on her phone, shopping. Trying to ease the pain, what happened next would go down in East High History though.

Taylor asked Gabriella why she came back, and the brunette looked at Troy and smiled "I just couldn't leave Troy, I thought I could but I don't want to miss our last months at school together, prom, and the musical" she said kissing Troy's cheek.

Sharpay heard this and snorted, "No you realized you weren't good enough for Stanford and came running home" Sharpay said loud enough for Gabriella to hear.

"You treat Troy like some dog, it's disgusting" she added taking a sip of her water and went back to her phone.

"What did you just say?" Gabriella said as Troy held onto her arm.

"Gaby leave it" he said "And Sharpay please don't do this right now," he said knowing shit was about to go down.

"Do what Troy?" she said looking surprised "I'm just telling the truth" she said.

Gabriella broke away from Troy and walked over to Sharpay.

"Say it to my face you passive aggressive bitch," she said as Sharpay stood up towering over the brunette in her pink heels and mini skirt.

"You left him you ran off to Stanford and left him here alone. You never take his feelings or dreams into account. It's all about Gabriella all the time and you think you can come back and everything will go back to normal? You are so fucking dense sometimes I swear I don't get the hype around you" she said.

Gabriella clenched her hands at her side, "I came back because I belong here with my boyfriend, did you think I would leave and he would be with you? You are a slut and an airhead that will never make it to Broadway. You live in this fantasy world. I'm sorry but your daddy can't buy you friends or a real life"

With that Sharpay slapped Gabriella causing the other girl to punch Sharpay and it soon turned into a catfight, both girls on the floor all eyes in the cafeteria on them.

"Shar stop" Troy said pulling the blonde off the floor holding her close noticing her nose bleeding "If you fucked my nose up Montez I will sue you and take all your pathetic family has" she yelled as Taylor pulled Gabriella off the floor, the brunette had scratch marks on her face.

"Shar baby I'm so sorry" this is all my fault Troy whispered in her ear as she relaxed in his arms.

Gabriella was shocked. Troy rushed to Sharpay instead of her, "Troy why are you comforting her?" she yelled, "She started this, she was really mean."

Sharpay had to bite her lip to keep from laughing "Why are you laughing you're crazy," Gabriella said hoping Troy would come comfort her.

"Oh, Gabriella you dumb bitch. Your boyfriend kissed me on the roof yesterday."

And with that Gabriella lunged for Sharpay again but Taylor grabbed her.

"She's lying Gabs, that plastic Barbie isn't worth it" she said.

Troy stood there looking between the two girls, "Troy is she telling the truth?" Gabriella said with a sinking feeling in her stomach.

"Gabriella, we need to talk." Troy said as the cafeteria started to buzz with what had just happened.


	3. The Boy is Mine

_**Must you do the things you do**_

 _ **You keep on acting like a fool**_

 _ **You need to know it's me not you**_

 _ **And if you didn't know it's 'cause it's true**_

 _ **I think that you should realize**_

 _ **And try to understand why**_

 _ **He is a part of my life**_

 _ **I know it's killing you inside**_

 _ **You can say what you wanna say**_

 _ **What we have you can't take**_

 _ **From the truth you can't escape**_

 _ **I can tell the real from the fake**_

 _ **When will you get the picture**_

 _ **You're the past I'm the future**_

 _ **Get away it's my time to shine**_

 _ **If you didn't know the boy is mine**_

Ryan had gotten some ice for Sharpay's nose and was trying to get the bleeding to stop.

"Shar your face is going to be fine, I don't think your nose is broken." he said, feeling sorry for his sister.

"Yes Gaby, I kissed her yesterday," Troy said, deciding not to lie, "I was upset because you left. You didn't think about anyone but yourself and Sharpay comforted me," he said looking over at the blonde. "I regret kissing her, but she was here for me when you weren't," he added.

Gabriella had her hand on her T necklace, "So what are you breaking up with me?" She asked, "Did I come back for nothing?" She said as Troy looked between the two girls.

"I don't know what I want. I just need time to think," he said grabbing his backpack and leaving the cafeteria.

"Looks like it's on Montez," Sharpay said deciding to go home for the day. She needed to get in bed and ice on her face.

Gabriella was left stunned, she didn't know where she stood with Troy now. If they were together or if he wanted to be with Sharpay.

"Taylor am I selfish?" She asked sitting next to her friend.

Taylor sighed, "Gabby you know you are my best friend, but in this moment yes, you are. You can't expect the world to stop when you decide to leave, and everything be perfect for you the second you come back. I'm proud of you and what you get to do at Stanford, but you did some damage." Taylor knew she sounded mean, but she didn't want to lie to her friend. "You did this over the summer and it worked out. Did you think you could do it again and everything would be sunshine and rainbows?"

Gabriella bit her lip realizing her friends and Troy were slipping away and for once maybe it wasn't Sharpay a fault, it was hers.

Troy got to his truck and watched Sharpay walk to her car, Ryan getting in the driver's seat. He was shell shocked to say the least, and felt like the biggest douche canoe for how he treated Sharpay, the one person who was truly there for him, and yet again he took her for granted. "Fuck!" He said hitting his steering wheel watching the pink convertible drive out of sight, he never meant for things to end up like this. He never expected Gaby to come back, but in that moment, there was one girl on his mind and it wasn't the one who left him broken. It was the girl whose heart he'd broken too many times to count.

He got out his phone and texted Chad.

"Dude my house, now. We are ditching the rest of the day. I need to get this shit sorted out, bring beer."

30 minutes later the two were in Troy's room with a few bottles of beer trying to figure out Troy's next move.

"Dude, you know I'm not Sharpay's biggest fan, but you may have ruined a good thing." he said taking a sip from the bottle. "I've seen a different side of Gabriella this year and even Taylor doesn't like it, and that's her best friend," he said surprising Troy.

"I never thought I would see the day Chad Danforth would be on Sharpay Evans side," he said, "I mean, I've always known there is more to Sharpay than meets the eye, and yesterday, she was more supportive in 15 minutes than Gabriella has been in months. I think I know the answer, I'm just afraid to admit it to myself," he added.

Sharpay was in her room watching Marie Antoinette and icing her nose while Ryan sat next to her with a bowl of popcorn.

"I still can't believe she hit you," Ryan said, "I mean I knew it would happen eventually, but damn."

Sharpay rolled her eyes, "She's just lucky my manicure isn't fresh, or she would have been in a world of hurt," she said with a laugh as her phone screen lit up with Troy's name. She hit ignore, "I refuse to speak to him right now," she said throwing her phone to Ryan. "He humiliated me this morning and he needs to suffer for a bit before I even begin to consider forgiving him. Or he needs to make some grand gesture," she said theatrically waving her hands.

Meanwhile Gabriella was sitting in math texting Troy over and over trying to reach him. Trying to get to him before Sharpay, did but he wouldn't answer her. The rest of the day went on uneventful everyone looking to school the next day wondering what would happen.

But, at the Bolton household, Troy was planning something so elaborate, he knew he would need some help from an expert. he picked up his phone and dialed a number.

"Hey dude it's me, I need your help with something, and I need it to be your most over the top crazy production you've done yet," he said as Chad gave him a thumbs up.

"I'll be over in 10," the voice on the line said before hanging up. Now the plan for Troy Bolton to win Sharpay Evans was in motion and it was going to be, well as she would say, fabulous.


	4. Prom?

Troy knew that whatever he did to get Sharpay back had to be epic, so when Ryan agreed to help him with an over the top promposal and apology, the girl's brother couldn't turn him down. Troy's phone kept going off with texts from Gabriella, but he didn't answer them. He couldn't deal with that situation right now, not when losing his dream girl was on the line.

As he looked at the stage and tried to see how to make his vision come to life, Ryan said, "So I'm thinking we do it in the auditorium lots of pink and flowers."

Troy said looking at Ryan, "I just want her to be so happy when she see's it. You know your sister means a lot to me."

"I know."

"Okay, time to get to work."

Gabriella was getting frustrated that she couldn't reach Troy. Maybe she shouldn't have come back after all. She was at school a little late finishing a paper when she saw that Troy's car and Ryan's were in the parking lot. She went back inside and scoured the halls until she found them. When she saw the twinkle lights that spelled out _prom with me?_ she was so excited. "He's asking me to prom!" She said a smile forming on her face. She thought to herself, _See? You worried for nothing. Sharpay is still not a threat_. She raced to her car to go home and change and wait for Troy to text her.

Meanwhile at the Evan's residence, Sharpay found herself alone. She couldn't find Ryan anywhere and she sure wasn't going to text Troy yet. She wanted to let him sweat for a bit. She was about to go find something to eat for dinner when her phone vibrated with a text from Ryan: _Come to the auditorium ASAP - it's important_. She rolled her eyes, knowing her brother was as dramatic as she was. _This better be good_ , she texted back, grabbing her purse and starting the drive to East High.

At the Montez residence, Gabriella was sitting on her bed staring at her phone, waiting for a text from Troy. She knew he was going to be texting at any second. She looked at the clock and sighed. "Guess I'll get comfortable," she said to herself, turning on a movie and looking at her phone every few seconds.

Sharpay pulled up to East High and saw Ryan waiting by the entrance. "Where's the fire?"

"Just follow me," he said, leading her down to the auditorium. When they got to the doors, Ryan paused before opening them. It was dark and Sharpay couldn't see.

"Okay, this is turning into a horror movie. Am I about to get murdered?" She was about to turn around and leave when the lights turned on to reveal Troy Bolton standing on the stage in a suit with a hot pink tie with tons of pink peonies and roses, "What is going on?" She asked, walking towards the stage, not being able to help smiling.

Troy pulled a rope and a sign came down that said _Will You Go to Prom With ME?_ in pink twinkly lights with glitter. "Oh my gosh!" She said, looking at Ryan who was sitting in the audience seats recording the whole thing on his phone. She asked him, "Did you help him with this?"

"Guilty," Ryan admitted with a laugh. "Where do you think he got that pink tie and the glitter and twinkle lights?"

Sharpay walked onto the stage and Troy began to speak. "Sharpay, I am so sorry I didn't tell you Gabriella would be coming back. I was in shock and I was a coward for not telling you." He took both of her hands in his. "When everything went down in the cafeteria today, I ran because I didn't know what to do. I was stuck between my past and what my future could be, but I had a beer-fueled heart to heart with Chad and it was clear that even though Gabriella is back, everything you said to me on that roof is still true." He grabbed a rose and handed it to her. "Sharpay Evans, will you be my date to prom and will you also go out with me?" He asked, hoping all of this wasn't for nothing.

Ryan was still recording and yelled out, "Say yes! I have glitter in places no one should have glitter from all of this."

She looked at Troy "Well, I was going to make you suffer for a bit, but this is amazing. Yes, I will go to prom with you and I will go out with you." She saw Troy's face relax so she pulled him in for a kiss, realizing being without him for this day made her miss him.

"Get it!" Ryan yelled, still recording.

"Ryan, will you shut up?" Sharpay yelled and the three of them broke into fits of laughter. She said to Troy, "Well since you are dating me he is part of the deal."

"I think I can deal with that. He's actually pretty cool," Troy said.

"But one thing I want you to do break up with Gabriella tomorrow. I want to sit with you at lunch, walk to classes together, and ride to school together. We only have a few weeks left, but I want to make the most of them," she said making her signature pouty face that never failed.

"Oh, the pouty face I remember that from last summer! You know I can't say no to you and I want all of that, too. I promise tomorrow I'm ending it," he said.

"Lets get out of here. I'm famished and need some dinner" She took his hand and led him off the stage

Ryan yelled, "I'm texting you the video!"

Sharpay got in Troy's truck and got out her phone opening the video Ryan sent her. "I'm so glad he recorded this" She loved the fact she could have this moment with her forever. "I'm posting it right now" She uploaded it to Instagram with the caption _I have the best prom date in the world_ with a pink heart emoji.

"I'm thinking we could get some pizza and go to my house," he said. "We can sneak in. My parents should be asleep. We are going to be so tired for school in the morningm but I don't care."

"I think spending time with you is worth losing some beauty sleep, babe," she said as she pecked his cheek.

Gabriella was still waiting when her phone dinged with a notification. She quickly picked it up and instead of a text from Troy, it was an Instagram notification that Sharpay had posted something. "Well this should be interesting," she said, opening the app and playing the video. When she saw what was happening, it felt like someone had stabbed her in the heart. The promposal wasn't for her, it was for Sharpay. "What the fuck!" She watched the video again. How was she supposed to go to school tomorrow and face everyone knowing Troy would be breaking up with her? She went downstairs to talk to her mom and they decided she would finish out the week and then she would go back to Stanford and never look back.

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 **A/N** : A big thank you to my beta, **Sophia Anne Moore**!


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